


Daddy's Girls (A Wincest Father's Day)

by MothMeetsFlame



Series: Holidays with the Wincesters [9]
Category: Supernatural
Genre: Aftercare, Anal Fingering, Anal Sex, Angst, Blow Jobs, Bondage, Bondage and Discipline, Caring John, Cock Cages, Cock Rings, Crossdressing Dean, Daddy Kink, Dirty Talk, Feminization, Gags, Guilty Dean, Insecurity, Kissing, M/M, Makeup, Nipple Play, Objectification, PWP, Paddling, Panties, Parent/Child Incest, Plot What Plot/Porn Without Plot, Praise Kink, Punishment, Rimming, Rough Sex, Sammy is a Doll, Sex Doll, Sex Toys, Sibling Incest, Spanking, Wall Sex, Weecest, Whipping, Wincest - Freeform, light bloodplay, no regrets
Language: English
Status: Completed
Published: 2014-06-15
Updated: 2014-06-19
Packaged: 2018-02-04 19:29:18
Rating: Explicit
Warnings: Underage
Chapters: 5
Words: 11,353
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1790542
Author URL: https://archiveofourown.org/users/MothMeetsFlame/pseuds/MothMeetsFlame
Summary: <blockquote class="userstuff">
              <p>There are three things John wants for Father's Day. Dean and Sam are more than willing to provide them. </p><p>Ch1: Getting Ready (Plot)<br/>Ch2: Pretty Girl (PWP)<br/>Ch3: Baby Doll (PWP)<br/>Ch4: Bad Daddy (PWP)<br/>Ch5: Aftercare (Porn, hint of plot)</p>
            </blockquote>





	1. Getting Ready

**Author's Note:**

> I had some problems getting this written. My imagination took off when I thought about all the things I wanted to have the boys do, and the list got waaaaay too long, so I narrowed it down to three. I have to say that, from looking at my list, I am one kinky motherfucker. Who knew?
> 
> Fem!Dean is something I've been wanting to do for a while now, but the plot went on forever. My logic: Sam and Dean don't have anyone but their dad, so he deserves a few days to celebrate. Plot for day one, porn for days two, three, and four, then more plot to finish us off on day five (which kinda turned into a little porn as well). Comments are celebrated with happy dances of extreme joyfulness! If you have anything to say, I'm all ears. 
> 
> WARNING: Underage. Sam is 13 for this fic, and Dean is 17. Also contains incest. Lots and lots of incest between two boys and their father. There's also crossdressing, an underage human sex doll, and bondage/whipping/punishment/slight bloodplay/nipple play. If you don't like this stuff, don't click on it. I'm totally serious. Read the tags. I think I tagged everything, but if I didn't, you get the gist. 
> 
> Enjoy ;)

It was harder for him than he'd ever admit. He wasn't like Sammy. Sam could wear a burlap sack and make it sexy—had, in fact, but that was another story altogether—with his slim hips, and floppy hair that, mixed with his still-baby cheeks and wide eyes, gave him a feminine figure to put real girls to shame. His round ass and dime-sized rosebud nipples were just the icing on the cake.

Dean wasn't like that. He was too tall, and large in all the wrong places. His butt was pert, but not cute with little dimples that were the perfect target for the right tongue, and it was too firm, too large, and too rough for his too wide hips. His eyes were the brightest jade green he'd ever seen, but other than that, there was nothing else he could see that could justify his father’s and brother's attraction to him.

It was even worse after Rhonda.

She'd opened the door to a whole new level of self-hatred.

It was the panties that did it.

They were frilly, soft and tight in all the right places. It had been in his head ever since Christmas Eve when Sammy had gotten three— _three_!—pairs of pretty lace panties that started his collection.

He was happy for him. Really, he was. Sammy looked great in them, in anything really. When he'd come out of the bathroom in _those_ heels with _those_ panties and _that_ makeup, Dean's cock screamed with the torture of having to wait.

He was so caught up in the moment that he hadn’t realized until the next day that Sammy was the only one who's gotten them. Sure, their tastes were pretty different when it came to sex, but... was that really the reason their father hadn't shown a hint of wanting that from Dean? He knew he wasn't as pretty as Sam, but he was still pretty, right?

He studied his reflection in the changing room, noting every imperfection with dismay as he tried on the grey, then white, then pink, green, blue panties over his boxer-briefs.

They were amazing. Even though every line of his half-hard cock showed through them, they just felt... right. They drew away from the shoulders that were too bulky from grave-digging, the scars from being tossed around like a rag doll by poltergeist after poltergeist, the hard glint in his eye from all the evil he'd seen. He didn't have to be hard in these. He didn't have to be a Hunter. He just had to be pretty, not that he was doing all that great with what he could see in the mirror.

He wanted everything, though, not just the panties. Makeup was a must if he wanted to cover the few blemishes only he seemed to be able to spot in the mirror. Maybe some gloves to smooth over the calluses? A slip would work wonders for his masculine figure, transform it a little.

Then the thought crept back into his mind: what if he doesn't like it?

It wasn't all that difficult to imagine the thinly veiled skepticism John would have when he showed him his new purchases. Dean wasn't Sammy. His feminine qualities had gone right out the window around puberty. He knew his dad liked that. He liked Dean hard, liked the rugged quality of his voice when it was thick with sex. He said so, and Dean believed it wholeheartedly.

But what if that was all John liked? What if he didn't like that sometimes Dean dreamt about the feel of silk panties and mascara running down his cheeks while he gagged on his father's cock? He did have two boys, after all, and Sam was the only one of them who looked even halfway decent in anything that wasn't jeans and a t-shirt.

Dean pulled up the image of his father wearing the pair of panties that he currently held in his hand and shivered at the thought. The image definitely wasn't something that would hoist his anchor.

What if it was the same? What if John didn't like it?

Dean groaned in frustration and quickly checked out at the register before he lost his nerve. He ran for the bus, heading toward school, bags tucked safely into his backpack. If he was there when he planned, neither Sammy or John would know he’d skipped to go shopping.

He just wondered whether it was worth it.

 

* * *

"Oh my god, Dean!" Sam gaped like a fish at the sight in front of him, more in shock than anything.

Dean blanched and grimaced, a flash of shame crossing his face before turning the look into anger and yelling at him. “Don’t you ever knock?! Get the hell out!”

The door slammed in front of him, and Sam still couldn’t do anything but stare and try to wrap his head around what he’d seen. He wanted to laugh, but at the same time, he wanted to smack Dean in the head for not asking him for help.

“Dean?” he called, knocking on the door a couple of times like Dean had asked.

“Go away!”

“It’s not that bad,” he said through the door. “Promise.”

“I said, go away, Sam.”

“I can help you fix it. I mean, I know how to do it right, and I could show you, if you want. C’mon, Dean. Open up! I promise I won’t laugh.”

It took a few seconds, but Sam heard the door unlock and he breathed a sigh of relief that Dean trusted him with this enough to let him in.

Still, it was hard not to laugh at the sight Dean made sitting sullenly on the lid of the toilet seat. He wasn’t in anything but a pair of boxer-briefs, but the sour look on his face was perfectly accented by his futile attempts at applying makeup. There wasn’t anything that Dean had tried that he hadn’t royally messed up. His lipstick was ten shades too white, his eye shadow so dark it looked like two black eyes, his eyeliner too long, too thick, and too crooked, not to mention the foundation and blush which were both so gobby and concentrated that it would have been better suited in a carnival than on Dean’s face.

“It’s not so bad,” Sam said, grimacing to hide his smile.

Dean, however, wasn’t fooled. “It’s horrible.”

“I can fix it.” He left the bathroom and shuffled through his duffle bag for a few seconds before he was back. “Here,” he said. “Wipe all of that crap off.”

“Seriously, dude?” Dean asked incredulously. “Baby wipes?”

Sam just shrugged. “They work.”

It took Dean a while to get it all off, but five minutes—and four wipes—later, his face was clean and ready for Sam’s genius.

He grabbed the makeup bag and took out the foundation, mixing it to suit Dean who was two shades darker than he was. Before he could even touch his brother’s face, though, Dean pulled back and looked at him skeptically.

“I don’t know if I wanna do this,” he said.

Seriously? Dean was an idiot. “Says the man who spent who knows how long locked in the bathroom trying to do _this_ —wrongly, I might add. Now that you have someone here who actually knows what he’s doing, you don’t want to do it anymore? I don’t think so. Sit,” he ordered when Dean tried to stand.

Dean sunk back down on the toilet seat, frowning, but not moving against Sam when he started applying the foundation.

“What _is_ all this?” Sam asked, motioning to the three bags sitting on the sink counter.

“I wanted to dress up for Father’s Day,” Dean said quietly.

Sam smiled, happy to know that he wasn’t the only one who had the weird feminization kink. He’d been starting to wonder if something was wrong with him.

“It’s just…” Dean trailed off.

“Just?”

“I don’t know. It’s hard. It’s… not like it is for you. I mean, you’ve been doing it for as long as we’ve been doing it. It never bothered you, but… I dunno. It’s hard.” Dean shrugged.

Sam finished with the foundation and rummaged through the bag for the eye shadow and his brush set. “You’re stupid,” he said plainly. “Seriously.”

“What?”

“Close your eyes.”

Dean did as he asked, and Sam dipped the eye shadow brush into the cream-colored container, getting just enough on the tip to do the base. He brushed it on quickly and chose another color, concentrating on his brother’s eyes while he spoke. “I never dressed like that before Christmas Eve.”

Dean scoffed.

“No, seriously. I mean, yeah I wore, like, girly stuff sometimes, but it was all dress-up stuff for Easter or Saint Patrick’s Day or something. I was a bunny, then a leprechaun.” He switched colors and kept going. “I was even Cupid one year, but those were just _costumes_. Christmas Eve was the first time I ever wore any of that stuff when it was regular clothing. It was totally different.”

At least Dean wasn’t scoffing this time.

Mascara. Eyelash curler. More mascara. “Okay,” Sam said, stepping back slightly. “Open.”

Dean opened his eyes, and Sam nearly gasped at how freaking _green_ they were. The pink and gold really defined them and, holy crap, just imagining what Dean had bought…

He was well on his way to getting hard.

“Well?” Dean asked. He cast his eyes down self-consciously, something Sam was decidedly against. Those pretty eyes should never be covered up.

Sam used the side of his finger to lift Dean’s chin until their eyes met. Slowly so he could savor the moment, he brought their lips together. It was tender and sweet, slightly wet though he didn’t use tongue. Dean’s lips were thick and soft, the sweetest Sam had ever felt. When he pulled back, he was surprised to find himself pulling in a ragged breath.

“Needed to do that before the lipstick. We wouldn’t want it to smear,” Sam said, voice shaky. He took in another breath and righted himself before dipping back into his makeup bag for the next set of supplies. “Hold still,” he said, brandishing the lipstick—pearl; he didn’t really want to overdo it. “And no talking.”

Foundation—check.

Eyes—check.

Lips—he wiped the thin line that went beneath the bottom lip—check.

Cheeks—

Sam grabbed the blush brush and set to work.

“I was terrified,” he continued. “I knew Dad liked it, or else he wouldn’t have got ‘em for me, but I almost didn’t come out of the bathroom because I was scared of what you’d think.”

“Me?” Dean asked, shocked.

Sam nodded. He glanced up and made eye contact with Dean, loving the way his green eyes sparkled with confusion, then understanding.

“You didn’t think I’d approve,” Dean surmised.

He shook his head in agreement. “It freaked me out at first that you wouldn’t like ‘em. It’s something that could’ve ruined everything, you know? But then I realized that I had at least one person who approved, and I thought, _if Dean doesn’t like them, he can suck it_.” Sam smirked. “So I wore ‘em. And I liked it. And Dad liked it. And _you_ liked it.”

Dean sighed. “But that was _you_.”

“So?” Sam asked, stepping back to admire his masterpiece, deciding it was perfect, and putting all of his stuff away.

“So… I’m not like you. I’m not…”

“Pretty?” Sam finished for him.

Dean grimaced and looked down again.

Sam brought his chin back up and looked him straight in the eye. “You’re an idiot,” he said. “Trust me. If Dad doesn’t like you all prettied up like this, he’s an asshole.” Then he added. “I’d kiss you if it wasn’t for the lipstick.”

Dean smiled, still not completely convinced, but well on his way.

“C’mon,” Sam said. “It’s time to show me what you bought.”

 

* * *

Father's Day.

John shivered at the implication, cock hardening in his pants through no force of his own when he thought about all of the possibilities. It was a tradition—inasmuch as two years could be called a tradition—that both boys surprise him with something unexpected.

Usually, that meant sex in many shapes and forms.

Last year, he popped his bottom cherry. The year before was Sam's first DP. This year… whatever it was, it was sure to be good.

They were all pretty active in their sex lives, most of their fetishes and kinks already out in the open. He didn't think there was a single thing that they could really surprise him with, though he wouldn't be surprised to find it risqué. Considering he was a mid-thirty-year-old man who slept with his two underage children on a regular basis, there wasn't really anything that could compare in the risqué department, though he had a few ideas.

He was two days out when he started making a list of everything he wanted for Father's Day.

He was one day out when he'd narrowed that list down to three things: a Sammy doll, a nice whipping scene, and cross-dressing Dean. For all they'd played around, those were just a few of the things they'd yet to try.

He wasn't so sure he'd get any of them though. Sammy was too expressive to be a doll. There was no way he was going anywhere near his boys with a whip—and they probably wouldn’t feel comfortable whipping _him_ , though the idea was strangely appealing. And Dean wasn't into the whole fem kink thing. They both loved Sammy when he dressed up for them, but Dean wasn't that kind of kid. He was too mannish for that. Sure he had the perfect lips for it, and the subtle curves of a women, but John didn’t think that Dean would get any satisfaction from it, and if Dean wasn’t really into it, there was no real appeal for him either.

At six hours before he reached the house they were squatting in, John called the boys to let them know he was close.

“Hey, Daddy,” Sam said happily into the phone. Thirteen years old, and he still called him Daddy.

John wasn’t loath to admit that it turned him on.

“You almost home? Dean and I have a surprise for you.” His smile could be heard through the phone, and John’s anticipation grew.

“Six hours, give or take. You boys staying safe?”

“Yep. Pastor Jim called yesterday and told me to tell you about a Hunt in Indiana, but I told him you were going to be busy for the next few of days. He said he’d call Caleb.”

“I’m gonna be busy?” he asked.

“Mmm-hmm. You, me, and Dean are gonna need some time to recuperate.”

And fuck if that didn’t have his imagination in shreds with the implications.

It didn’t take him the full six hours to reach his destination. Four and a half hours later, he pulled into the driveway of the somewhat-decent house he’d found for him and his boys to squat in, far from prying eyes, and walked the dozen paces to the front door. It was reminiscent of his cabin in North Carolina, and he had a sudden flash of fucking his youngest hard and deep against the back porch—something that was definitely going to happen before they left.

He didn’t knock, just unlocked the front door and went inside, stomping the mud off of his boots and flicking the light on before making his way to the bedroom.

Shock. Betrayal. Anger.

Emotions flitted through John, fast as lightening at the sight before him.

They’d talked about bringing another person into the fold—sometimes a man, often a woman—but it was too risky. Not only that, but the thought of having to share his boys with anyone else, man _or_ woman, had his possessiveness flaring to life in ways that endlessly satisfied his sons. To think that Sammy had gone against him, especially on today of all days, hurt him in ways that he couldn’t even comprehend.

“Hi, Daddy,” Sam said, lifting his head from the woman’s neck. She made a small whimpering noise and fisted her painted hands in the sheets as arousal flushed through her. “Wanna taste?”

John didn’t know what his face looked like, but the way Sam’s expression went from lustful to fearful in the space of a few seconds would have been comical had it not been for the rage flooding through him.

“What the _hell do you think you’re doing_?!” It was pain, knowing that Sam would do this. They weren’t exclusive or anything. Both Dean and John slept with other women, sometimes other men. Sam had had a couple of experiences also, but bringing someone _here_?

“I-” Sam floundered for a response.

John saw a flash of movement behind Sam and took another look at the woman on the bed, now curled around herself, tucked into a ball, shivering with fear, and felt a pang of guilt for scaring the poor girl. “Shit,” he said. She was young and pretty, with light brown hair waving around her delicate face. The sleek negligee was something he would have found insanely attractive in any other set of circumstances. “Fuck.”

“Fuck you,” finally came the reply from his youngest.

Sam’s anger matched his in its intensity, and John reeled back in surprise before setting himself firmly against him. _Sam_ was the one who was wrong in this situation, not him.

“What did you say to me, young man?” John said, voice hard, giving his son the opportunity to correct himself.

“I said, _fuck you_.”  He spat the words.

“That’s it, I’m gonna—”

“Will you both please stop it!”

John blinked, taken aback. He hadn’t noticed Dean anywhere, but that was definitely his voice with its familiar tinge of apprehension.

“I –I’m sorry. It’s my fault,” Dean continued, while John glanced around, trying to find his son. “ _I_ was the one who did this, not –not Sam.”

Holy fuck.

“Dean?” John asked, staring skeptically at who he’d assumed to be some strange woman in his bed.

“I wasn’t sure if you’d like it,” he whispered. Fuck, the boy sounded heartbroken, and Sam glaring daggers at him made sense now.

Dean’s legs curled under him, and he glanced away, absentmindedly chewing on his bottom lip. Unlike Sam’s put-on innocence, this was real, completely genuine. Dean was _shy_ for christssake. How the hell had he managed to screw this up so completely?

“I’ll… go change.” Dean didn’t look at him as he crawled out of bed, heading straight for the bathroom.

“You’re not going anywhere,” John said, wrapping his arm around his son’s slender waist and pulling him down so he was sitting right on top of John’s stirring cock.

“You –you don’t have to…”

“To?”

“To like it. I mean, it was just something to try, not like it really means anything.”

John scoffed. Of course it meant something. That Dean had kept it from him for so long pretty much guaranteed it.

Thinking that the scoff was aimed at him, Dean flushed and looked down in shame.

“Settle down, Sam,” John said, when his youngest looked like he was on the verge of pulling Dean away from him and tearing his eyes out. “Just listen for a minute. I think we all got a little mixed up.” Then it was his turn to blush. Now that he thought about it, it seemed kind of stupid. “I, uh… Well…”

Sam glared. “Get on with it.”

John ignored his snarky attitude and continued. “When I walked in, I thought you decided to go ahead and add a fourth person, like we’ve been talking about.”

Sam’s brow furrowed in confusion. “But you said no.”

“I know. That’s why I was upset.”

It took a second for Sam’s brain to catch up, to realize where everything had gone wrong, but when it finally did, John was surprised to find him laughing.

“Sam?” Dean asked, still sitting awkwardly in his father’s lap.

“Dad… he thought…” he said between chortles. “he… Dean… he thought… _you were a girl_.”

“What?”

John rolled his eyes at Sam’s amusement, and turned to face his eldest. “I wasn’t mad because of this,” John said, trailing his finger down the thin lacy nightie Dean had on, and dipping it underneath to toy with the front of his soft panties. “I thought Sam brought home a girl for us to play with.”

“Really?” The hope really made Dean’s eyes sparkle. Damn, he was pretty.

John nodded. “You know I don’t like sharing you, especially when you’re all dressed up for me.” Dean gasped when John’s finger found its way inside of him. “Your pussy’s all wet for me, baby,” he whispered in Dean’s ear. “You been waiting like a good girl for Daddy?”

“Yes,” he squeaked breathlessly, and fuck if he didn’t sound like a girl in that moment.

With his other hand, he pulled Dean’s chin toward him and brought their lips together. Cherry and lipstick and _Dean_ assaulted his senses in an arousing sensation that sent lust coursing through him.

Sam was right, they were going to need a few days.


	2. Pretty Girl

**Summary for the Chapter:**

> Dean's a slut for Daddy's cock.

**Notes for the Chapter:**

> And a bit of porn to tide you over until tomorrow :) Here's cross-dressing Dean with John.

Dean was still trying to wrap his head around everything when his father’s voice echoed in his ear.

_““Your pussy’s all wet for me, baby. You been waiting like a good girl for Daddy?”_

_I, uh, I…_ “Yes,” he squeaked. It was the same voice Sammy had been teasing out of him every since he’d dawned the wig.

 _Holy shit, De_ , he’d said. _So pretty._

And Dean had seen his cock tenting his pants then as he adjusted the wig on him so it would stay in place. He’d seen himself in the mirror, and… Sammy was right. He was _pretty_.

The finger inside of him crooked, and he yelped in surprise at the sudden rush of pleasure as someone finally paid attention to his prostate.

Dean’s eyes slipped closed. His mouth parted. His hips rose of their own volition.

“That’s right, baby girl,” John continued, oblivious to Dean’s meanderings. “Let Daddy take care of you.”

His other hand trailed down his front, hesitating at the hem before lifting it enough to toy with his nipples. John was thrilled at the harsh panting noises he was eliciting from his son at the movement, but it wasn’t enough. He wanted his girl practically _writhing_.

“C’mon, princess,” he said, pinching hard and loving the low keening it produced. “I wanna taste your pussy.”

Sam gasped from behind them, shocked at the abrupt change in the room. Not thirty seconds ago, he was ready to tear his father’s eyes out. Now all he wanted was his father to hold him up against the wall and fuck him into oblivion.

“You coming, Sammy?” John asked, looking at him while he flipped Dean back on the bed and absentmindedly parted his legs. “Your sister’s waiting.”

John turned back to Dean, and sucked in a shocked breath when he caught sight of his second surprise: a tightly-fitted cock cage.

They’d talked about it. A lot.

Neither of the boys really showed much interest, though John thought he might try a chastity device when they were a bit older. Just seeing it on his eldest drove him crazy.

The pink plastic hugged his straining cock in its confines, keeping it from hardening with any degree of success.

A small hand touched his shoulder—Sam, getting his attention—and it wasn’t until then that he realized he’d been staring slack-jawed at Dean’s caged form. The small hand wrapped around his shoulder and pulled him in for a kiss, hard, wet, and steaming, breaking his line of sight. Sammy’s tongue twisted its way inside his mouth, assaulting his senses in the best of ways.

John lifted him by the thighs and nearly wept at the sensation of Sam’s lithe frame against him, canting his hips up to rub their clothed cocks together, the stimulation perfectly frustrating in its intensity.

Sam was the one to pull back first. With a small smile, and a lick of his swollen lips, he parted their kiss, laughing when John looked at him grumpily.

“Here,” he said, holding out a small key.

John was confused at first, but realization dawned on him.

“De said that, if you don’t like it, to let her out.”

A thrill ran through John at the word _her_.

“She won’t be mad.”

Then Sammy was off of him and ducking into the hall without so much as a backwards glance, leaving him alone with Dean.

He looked back at his son on the bed, the one he had to try to find beneath the cover of makeup and lingerie. John glanced back at the key in his hand, suddenly overwhelmed with the responsibility he was given. It was one thing to mess around with this orgasm denial stuff, quite another to go this far into it.

“You sure this is what you want?” he asked

Dean bit his lip—wetness showed on his lips; _ohGod_ that was hot—and nodded, looking up at him between thick lashes.

“One week,” John said.

The relief on Dean’s face was enough that he knew he’d made the right choice.

“Maybe longer, if you don’t behave.”

The smirk that played on his son’s face was one hundred percent Dean in that moment, and it held a promise that that one week would almost definitely be extended. But then the smirk turned a little unsure—something Dean _never_ was in bed—and he looked down, hiding his pretty green eyes beneath his carefully tousled bangs.

“None of that,” John ordered. He sat on the edge of the bed beside Dean and lifted his chin until they were eye to eye. Then he crushed their lips together in a bruising embrace while Dean whimpered beneath him. “Keep your eyes open. I wanna see them when I fuck you.”

John didn’t miss the goose bumps that crawled down his arms, but Dean’s eyes held his obediently, even when he crawled over Dean and pulled his thighs down until they were flush against his.

“Told you I was gonna take care of you, pretty girl, and that’s just what I’m gonna do.”

He fingered the tight pink cock cage, smiling at the small grimace that showed on Dean’s face as his cock tried its hardest to swell. Then, without preamble, he shoved two fingers inside of his boy.

Dean yelped loudly and struggled to get away from the intrusion, but John’s hand held him in place while he explored, dipping his fingers inside, scissoring and stretching the clenching muscles until Dean was adjusted and ready for whatever John had planned.

“That’s a good girl,” John whispered when his baby had loosened up for him. “Your pussy’s all slick and wet, just waiting for me to take you. You want that? Want me inside of you?”

Dean couldn’t hold back anymore. “Daddy?” he squealed. “Daddy.”

“Shhh,” John soothed. “Settle down, baby. Tell Daddy what you want.”

“Want –want you in me Daddy,” Dean whispered shyly, his voice soft and feminine. “Want you to taste my –my pussy and…”

“And?” John prompted.

Dean blushed, but pressed on, his eyes swimming with tears of complete embarrassment. “I want you to fuck me.”

“I don’t know,” John teased. “I didn’t hear my baby girl ask nicely…”

“ _Please?_ ” Dean squeaked desperately, not even an attempt at keeping his composure. “Please, fuck me? Please? _Daddy_!” Dean screamed when John pressed firmly against his prostate, teasing spurts of precome from his flaccid cock. “Please, Daddy, please…”

“Of course, baby,” he said, smiling. “I love it when you’re all dressed up for me. You make your daddy proud, you know that?”

Dean nodded, suddenly shy again. “Am I… am I a good girl?”

John leaned down and licked across his lips, not caring that he was ruining the careful lines of lipstick he’d drawn on. “You’re a very good girl, princess, the best for me.”

He was rewarded with another spout of precome that he promptly licked up, pulling another cry from his boy.

“And good girls are sluts for Daddy.”

Dean’s eyes went wide, but he was up and out from under him immediately, pushing John down onto the bed and straddling him.

If there was one thing that Dean was, it was a slut for his daddy’s cock.

He pressed his lips chastely against his father’s, then lowered himself until he was eye level with the bulge of his father’s cock. Working quickly to release it, Dean ran his tongue over his lips in anticipation.

He groaned at the salty taste as he suckled the head of his father’s cock, smiling when he pulled off and caught a trace of lipstick around it. The sight fueled his arousal and he took his father again, sucking deeper and deeper until the cock was pressed back against his throat, but it had been a long time since it was sensitive to touch. This time, the muscles that contracted were his own doing, and he flexed them proudly to force the keening moans from his father as it stimulated the sensitive nerves.

Spit gathered in his mouth, slicking his way as he bobbed his head up and down, the friction just enough with his lips latched tightly around his father’s shaft. He loved the ache in his jaw as his mouth was stretched past the point of comfort, they way his eyes watered as the thick cock assaulted his gag reflex, the way he struggled to pull in a full breath of air as he shoved his father further and further down his throat, but the thing he loved the most was the moment when his father wasn’t able to hold back anymore, the moment when John tangled his fingers into his hair and fucked himself into his mouth.

With a hard pull, John yanked Dean off of him, meeting his son’s glazed over expression with his own. Only seconds away from orgasm, he gripped the base of his cock tightly, stubbornly holding it off.

“Want you…” Dean’s voice was rough with sex, but still soft in a way that surprised John. “Want you to fuck me, Daddy,” he said. “Please come in my pussy.”

The shy expression was back on his face, and how the hell was he supposed to say no to that?

“Of course, princess,” John whispered, twisting Dean underneath him and parting his son’s legs with his own.

He lined his cock up and teased the rim with his head, loving the way Dean gasped and twitched with every pass, his hair flinging out wildly around him and his nightie riding up to show his well-toned abdomen. He dipped down to taste the flushed pink skin, heated with sex.

“Da –daddy?” Dean gasped in shock as John’s tongue slithered his way into his belly button, leaving cold wet trails down his stomach.

“Yes, baby?”

“What are… Are you gonna fuck me?”

John smiled and pressed a kiss at his naval. “Not yet,” he said.

He took his time as he licked and kissed a path to Dean’s scrotum. Then he took the swollen sack into his mouth and suckled it until Dean was canting further into the touch, moaning a steady stream of _pleasefuckmepleaseDaddyplease_.

“I wanna taste your pussy, baby,” he said when Dean tried to pull him back up.

He let his tongue lick at the tip of his son’s soft cock, still caged and confined, one last time before going lower and plunging his tongue through the loosened ring of muscle.

“ _OhGodfuckDaddyplease!”_

He licked his way past the skin of his son’s taint and dipped his tongue in and out, watching as the muscle opened and closed to encompass him. With his two thumbs, he held Dean open and blew on his sensitive hole, filing away the scream Dean let out as the cold air assaulted him.

John ignored his baby’s cries and ate to his heart’s content. It was a different taste than usual—vanilla instead of cherry—but it suited his son well. Sex and vanilla and a wisp of perfume combined to compliment Dean’s own natural scent and, coupled with the taste of his son’s gleaming wet pussy, John’s cock wanted nothing more than to fuck into him hard and fast.

But he didn’t want to hurt his baby.

 

John spit, warm and wet, into his son’s now gaping hole before plunging three of his fingers inside, all wet with lube.

Dean yelped and pleaded— _fuckmepleaseDaddyfuckmeplease_ —as his prostate was hit repeatedly by John’s unyielding fingers, overwhelming him to the point of incomprehension.

Then the dreaded—amazingly wonderful—fingers were gone, leaving him empty and gaping, his need building up as his anticipation grew.

“You ready, baby?” John asked.

Dean nodded, eyes wide and glued to his father’s face like he’d been told. It amazed him more than anything else that he’d been able to keep his eyes open throughout all of his father’s teasing. “Yes,” he panted. “ _Yesyesyesyespleasefuck.”_

John smiled, leaning down to nuzzle his neck while he pressed inside of the tight heat of his baby’s pussy, slick and wet for him.

“ _Daddy!”_

“Fuck! So tight for me, baby. Such a good girl.”

He thrust in steadily, hilting himself in one move while his son screamed and writhed beneath him. It wasn’t a scream of pain, but of pleasure, so John didn’t even pause, choosing instead to pull out to watch his son’s hole quiver as it was suddenly emptied before thrusting in again, hard and unrelenting, filling his boy up with his thick cock.

Dean’s inhibitions were released then with the feeling of his father’s cock inside of him, and the extent of his vocabulary was finally realized as colorful expressions flew past his lips, filth spilling from his pretty little mouth.

“Fuck! Fuck my pussy, Daddy. Hard. _Yes_! Fuck. Oh, God. Need you, Daddy. Need you to fill me up, fuck me harder— _uh_ —there, Daddy, right there. Want you to fill me up, stuff me full of your come. Want it leaking out of me, please. _Ah_! So good. I’ll be such a good girl for— _fuck_ —for you, Daddy. Please. Want your come. Please, Daddy? Can I— _uh_ —can I have it?”

With that question, John couldn’t hold it in any longer. He slammed in hard and came with a grunt deep inside his son’s tight ass. The rolling orgasm took hold of him and made his head float while Dean screamed in victory beneath him.

His hips absentmindedly thrust him through his orgasm, waves of pleasure shooting through him with the movement until his cock was completely spent of every last drop of he was capable of producing.

John moved to pull out of his son, but Dean grabbed his hips tight and held them.

His baby bit his lip, changing from the cockslut who screamed for his daddy’s come to the shy boy who demurely asked his father if he was pretty.

“What’s wrong, princess?” John asked.

“Nothing,” Dean said quickly, but the hands that stayed firm on John’s hips told a different story. “It’s just, um… Can I –can you stay in me, Daddy? I…”

John smiled. “You wanna be my little cockwarmer?” he offered. “Wanna stay stuffed full of Daddy’s cock?”

Dean nodded, still shy.

“Look so good when I’m filling you up.”

Suddenly, John flipped them over so Dean was straddling him, their chests pressed tightly together, John’s cock still inside of his son’s leaking ass.

Dean blushed again, his cheeks pinkening, blending perfectly with his soft green of his eyes.

“Um, Daddy?” he asked quietly.

“Yeah, princess?”

“After this, can we… Will you play dolls with me?”

John’s confusion was plain, but that didn’t keep him from muttering, “Sure, baby. Anything you want.”

Dean’s smile was brilliant, showing off the straight whites of his teeth. “Thank you, Daddy.”

“No, thank you, my pretty girl.”

John lifted his head to capture his son’s bottom lip between his teeth. Already, he could feel his cock twitch, wanting to be able to fuck into the velvet heat of his baby’s ass.

 _Later_ , he thought, biting down hard and licking his way into Dean’s parted mouth.

There was still plenty of time to play.

**Notes for the Chapter:**

> Check back tomorrow for the next chapter, featuring Sammy and John (and possibly some Dean on the side).


	3. Baby Doll

**Summary for the Chapter:**

> John promised to play dolls with Dean. It's too bad Dean has something else to do. Oh well. Looks like John will have to play alone.

**Notes for the Chapter:**

> Sorry! So, so, so sorry that it's late :( My internet has been out since Monday night, and it's STILL NOT WORKING!!! I invite you all to join me in my rally against the phone company. Time and place TBD. 
> 
> Anywho... Here's chapter three of the fic, brought to you by my bestest friend in the whole universe (thank you, Sarah!!) who has allowed me to borrow her kitchen table and her internet to post porn. Doubly sorry for the lateness. Enjoy ;)

_Will you play dolls with me?_

John was more than a little confused at the question. Obviously, he knew what dolls were and how to play with them—that wasn't why he was confused. The confusion came from why Dean wanted to play dolls in the first place.

Traditional toys were never something his boys really had, and this was different in a hundred ways, but something about the tone Dean took—the tone that wasn't self-conscious and shy, and _fuck_ sexy as hell—said there was something really big he was missing.

If he really thought about it, he could certainly see the appeal in role playing.

Watching as Dean played in a cute outfit with his tiny little dolls, dressing them in tiny little outfits, while his slim waste and wide hips showed the natural curve of his ass in tiny little panties, cock cage shaking every so often as he scoot across the floor, hair done up in pigtails, curling down and framing his face with wide green eyes and sex-swollen lips—oh yeah, there was a definite appeal.

Then John would say, _why don't you come sit on Daddy's lap to play?_

And Dean would bite his lip and look up at him with those green eyes and pink, embarrassed cheeks and say, _okay, Daddy_.

And he would crawl onto his lap, pert ass rubbing right against his rapidly hardening cock, wiggling and shaking as he played with his dolls.

John's cock was nearly hard now, still nestled deeply inside Dean's ass. His baby could feel it, John knew.

"Daddy? You ready again?" Dean asked in a small voice.

"Yeah, baby."

"But..." He trailed off and looked up with pleading eyes that made John want to give him the world. "But, you said you'd play dolls with me."

John held in his sigh. There was a time and a place for role playing, and now was not the time. That particular fantasy was a slow-burner. It took time and time and more time to get going, nice and slow so he could play with his princess the way she should be played with.

Now, though, he wanted nothing more than to slam into the wet pussy that surrounded him and pound his baby's ass until he screamed for more.

"Not now, princess. We'll play later. Now, Daddy wants to use you up, hear you scream while you ride me like a good little girl."

Dean pursed his lips, and the look that followed was so contrary to his previously demure one that John was nearly sure he'd imagined it. Dean smirked, eyes sparkling with mischief.

"Oh, I think you'll be happier playing dolls with me, Daddy. ‘Sides you promised." He pouted, bottom lip jutting out in a way that made John want to pull it into his mouth and bite it.

So he did.

"Okay, baby," John answered as Dean sucked the soon-to-be-swollen lip into his mouth. "Let's play."

Dean grinned and led him out into the hallway, passing his own bedroom and heading straight to Sammy’s. The glance before Dean opened the door was nervous, and it filled John with apprehension.

…which completely went away when he realized just what playing dolls meant.

Sammy lied perfectly straight on his bed, his own makeup much more subtle than his brother’s. There was a slight sheen to his cheeks, which were pink with blush, and his hair had been fixed so it fell on either side of his face in perfectly straight lines until it touched the sky blue baby doll dress he’d gotten for his birthday. He was still, so still that John was sure it really was a Sammy doll—until he made out the subtle fall and rise of his chest.

“You like her, Daddy?” Dean asked, no longer shy now that it was Sammy on display.

John’s cock hadn’t gone down any since he slipped out of Dean’s hot pussy, but even if it had, it would have been back now. “I love her, baby,” he said, voice rough.

Then Dean was right in his ear, whispering so softly that it tickled and sent shivers down his arms. “Sammy’s your own personal fuck toy, Daddy, a hole for you to use however you want. Baby doll is soft and ready for you, so don’t worry about breaking it.”

John felt wet tongue on his neck.

“I’d try the mouth, Daddy. It parts just right for your thick cock, no gag reflex to trigger or anything.”

The heat of Dean’s breath was gone then, and John was left wondering what the hell he was supposed to do.

“Wait,” he said when he heard the door open. “Where are you going?”

Dean smirked. “I’m getting your other present ready, Daddy. You have fun with your new doll.”

Dean left, and the closing door seemed too _final_ for John’s liking.

“Okay,” he whispered, stroking his cock once, twice, until it was at full mast.

He crawled on the bed and straddled his doll’s stomach, using his fingers to part its hair. The face was pretty and perfect, and John wanted nothing more than to try what Dean had suggested.

But first…

John felt the nipples through his doll’s dress and rubbed them slowly, pinching so he could hear—

 _Damn_.

John chuckled at himself for forgetting already as Sam staying perfectly still through a movement that would have had him whimpering any other time.

Sammy was his _doll_ , which meant that he wasn’t going to react. It was a little strange to accustom himself too, especially after his tryst with Dean in the other room.

John got off of the bed quickly and pulled his doll towards him, setting him up how he wanted him. Sammy’s head dangled helplessly over the side of the bed, face up to receive John’s cock.

Without any warning, John grabbed his chin and thrust into the wet heat of his doll’s mouth.

It wasn’t what he’d expected, not at all. Gone were the contracting muscles of his son’s throat. A sucking sensation was but a dream compered to the looseness of his doll’s mouth. His lips weren’t pulled over his teeth, and the light scrape on his shaft brought unexpected tingles of pleasure, while still not being enough.

He wanted, _needed_ more friction.

Instead, he thrust harder.

When Sammy sucked, John could feel when he pressed past the boy’s gag reflex.

This time, though, he could hardly even tell it was there. There was no struggle for breath when John fucked in roughly, deep in his throat over and over again while he relished in the looseness of his new doll.

But it was a hollow victory.

It had been a fantasy of his for a while, to have one of his boys as a fuck toy, but it wasn’t really what he expected. There were no whimpering moans, gasps, or grunts, no lusty eyes, slinky tongues, or blinks of surprised pleasure. It was silence and a wet passage. It was just one of the things that was better in his head than putting it into practice.

He thrust in deep and held it, waiting for—

—there.

Sam’s muscles moved just the slightest, testing to see whether he could breathe.

John held it.

He could feel Sam’s throat begin to tighten around his cock, struggling now without air.

John held it.

Sam tried so hard to stay still, John could tell, but his diaphragm betrayed him, twitching with need.

John held it.

Sam’s tongue moved against his cock—not a large movement, but subtle, so subtle that John wouldn’t have noticed had he not expected it.

John held it.

And there it was… Sam gagged around him, his muscles flexing in an attempt to rid himself of the intrusion in his throat.

John moaned in ecstasy and pulled out, letting his boy breathe. When it became steady and subtle, John continued, trying to tease more slips from his boy.

He trailed his finger down the baby doll dress until it touched the hard plastic of his doll’s cock cage. He gave the organ a flick, loving the half-concealed twitch.

Another flick.

Then he bent down and licked the slit of his doll’s soft cock, wiggling his tongue to tease the silky wet precome from his boy.

Sam’s breathing sped up, but the muscles stayed lax, something John promised to rectify.

John leaned back and pumped his own cock while he watched his son’s skin flush with need. It still wasn’t the reaction he wanted, but he had time.

Not bothering to lube himself up—Sammy had always loved his daddy to take him hard, without much prep—John slid into his doll’s hole and hilted himself roughly.

He fucked in and out of him, angling to hit his doll’s prostate, liking the slight clench of the muscles whenever he succeeded. John latched onto Sam’s hips and pulled his boy against him with every thrust, fucking deeper and deeper until he was too on edge to continue.

Then he pulled out.

He had a goal. He wasn’t going to stop now just because of his rising orgasm.

Besides, there was something he wanted to try.

“C’mon baby doll,” John panted his Sam’s ear, loving the goose bumps that formed on his doll’s neck.

John lifted the doll, limp in his arms, and held it tight against the wall, lowering it until the hot tightness of his doll’s hole was surrounding him again. He thrust experimentally, loving how the new angle stimulated the nerves on his cock, and then he was fucking deep and hard, taking his frustration out on his doll’s ass.

It wasn’t long before could hear the small gasps his son let out, could feel the small twitches as he begged silently with every fiber of his being to be allowed orgasm, but John didn’t relent.

He slammed in hard and fast, jarring his boy and making him forget that he was supposed to remain still and silent. Sammy grunted and moaned, tears falling from his eyes, and that was all John needed to come.

Hot seed spurted from his cock as he thrust into his boy’s now-clenching hole. It leaked around him, dripping down his thighs as John continued the punishing pace. He fucked his boy until he couldn’t and his spent cock slipped from Sammy’s loose hole.

He looked right into his boy’s swimming eyes, still holding him tight against the wall.

“Sorry, Daddy,” Sammy said. “I tried to be good.”

“You were the best, baby,” John said, licking his way into his boy’s eager mouth. He pulled back and nibbled on Sam’s ear, loving the small whimper it elicited. “Was trying to get you to scream,” he admitted.

“Bad Daddy,” Sammy said playfully, but his voice was thick with lust, and there was an undertone John couldn’t make out that had his limp cock struggling to harden. “I think you need to be punished.”

Oh yes, it was definitely struggling.

**Notes for the Chapter:**

> Okay, so to make up for my grievous mistake, I will grant a gift fic to the first two commenters on this chapter. 
> 
> Rules: There are no rules!! Just kidding. Rule #1: Has to be Spn. That's it. No more rules. Any pairing, and rating, any kink. 
> 
> Sorry again, people. Good news: the next chapter is going up in just a couple of minutes :) Stay tuned.


	4. Bad Daddy

**Summary for the Chapter:**

> Daddy was bad when he played with his doll. Sam and Dean think he's due for a punishment.

**Notes for the Chapter:**

> Today's chapter has arrived! Here's some PWP for your viewing pleasure. Enjoy ;)

It was another hour and a half before he could get his father’s cock to harden enough to slip on the cock ring. Dean couldn’t come again for an entire week, and Sam couldn’t for three days, but John couldn’t come until he’d been punished thoroughly.

That was a nasty trick he’d pulled, and Sam hadn’t counted on that, but it really didn’t matter what Daddy had done. Sammy would have punished him anyway.

Oh, he knew John had a pain kink, just as easily as he knew John loved when they played with his nipples and called him daddy and wore pretty panties while he fucked their tight holes. John was one kinky bastard. It was just another quality that happened to run in the family.

He led John by his cock to Dean’s room and ignored the shocked pause his daddy took in the doorway, pulling harshly to get him to move again.

Dean had done a great job transforming his bedroom into a makeshift dungeon. They already had the cuffs and holsters in the trunk of the Impala, but everything else he’d done—cloth-dimmed lamps, spotlights on the stand, and _holy fuck_ the chains—gave the place an ambience Sam didn’t think he’d be able to achieve.

Dean was out of his lingerie now, like Sam knew he’d be. It was still a shock to see Dean. His brother’s caged cock slipped through a hole in his leather underwear and was attached by small chains to his clamped nipples, his entire body surrounded by an undecipherable pattern of leather.

Sam absentmindedly thanked Dean for convincing him to do the whole cock cage thing because he definitely wouldn’t be able to last the entire scene without coming like he was supposed to. He still didn’t know if he could last the three days until Dean released him.

“You ready?” Dean asked.

Sam nodded. Time to get the show on the road.

“Good.”

Without warning, Dean grabbed John by his hair and forced him down to kneel on the stand. Sam came forward and strapped him in—wrists, elbows, knees, ankles—leaving only his hands free.

Dean lined John’s head up with the cock-shaped gag and forced him onto it while Sam strapped his head down. He was completely immobile.

John tried to talk around the gag, but Dean silenced him with a harsh look. He squatted down so he was at eye level with John, making sure to have his father’s attention before he continued.

“You okay with this?” he asked.

John gave a thumbs up.

“Okay. Give me a run through of your signals,” he ordered. “Slow down.”

John snapped with his right hand twice.

“Good. Remove the gag.”

John snapped alternately with his left and right hands.

 “Good. Stop the scene.”

John snapped with both hands.

“Good. Yes.”

John gave a thumbs up.

“Good. No.”

John gave a thumbs down.

“Good. For the rest of the scene, you will be completely immobile. Unless you use the signals, we will not stop. Understand?”

John gave a thumbs up.

Dean smirked then. “Go ahead, Sammy.”

That was all the warning he got before a loud crack sounded in his ear, followed immediately by a stinging pain on his back.

“Sammy’s been practicing. Haven’t you, Sammy?”

“Uh-huh,” Sam nodded.

Three more strikes of the whip and John was panting hard. His back was sore and red. Welts were beginning to rise on the soft flesh, but John’s cock was rock hard now and leaking steadily onto the floor, the cock ring holding his orgasm at bay.

“Weapons practice has been a lot more enjoyable, I’ll tell you that much,” Dean said. “How many does he get?”

“Fifteen,” the boy responded.

Dean quirked an eyebrow and Sam shrugged. They’d decided on ten to start.

“He kept trying to make me react when I was his doll. Flicked my cock and everything.”

Dean’s cock pressed itself against the walls of his cage at the image in his mind. Damn, he wished he was there for that. “Add five more,” he said instead.

“What for?” Sam asked, genuinely curious.

The whip struck again, and John grunted with the pain, his cock shooting another wad of precome onto the floor.

“For trying to talk earlier. Daddy knows that he’s not supposed to talk with a gag in his mouth.”

Sam smiled. The whip struck in rapid succession, and Dean hungered at the sight.

“Ten,” Sam said, bringing his arm down again.

Dean signaled Sam to pause while he ran his fingers over the raised flesh of his father’s back. John hissed around the gag at the prodding, but Dean didn’t stop. “Daddy’s been so good for us. Don’t you think, Sammy?”

“He still has ten more, Dean,” Sam reminded him.

“I know. If we don’t finish his punishment, he’ll never learn his lesson.” But Dean knelt down on all fours and took the swollen cockhead into his mouth.

Sam took John’s whimper as his cue to continue.

He counted each whip out loud, making sure not to strike hard enough to break skin. When he hit fifteen, John’s back was a crisscrossed array of sensitively swollen welts, pink with heat and glistening with sweat.

Sam set the whip down, taking a quick break to tongue at the sensitive flesh. It was hot and bumpy, and the small trails of sweat were salty under his tongue. He lubed up his fingers and shoved two inside of his father’s too-tight ass.

John yelled against the gag, but his hands remained clenched so Sam continued, forcing them in roughly, twisting and turning and scissoring them until he was loose enough for a third.

John screamed when he added another.

“Hush,” Sam ordered, using his unoccupied hand to scrape lightly against the welts on his back. “I don’t think Daddy’s learned his lesson, Dean,” he said, thrusting the three fingers inside, hard and fast, while John whimpered quietly.

Dean pulled off of his father’s cock, licking the slit once before standing. “I think  you’re right. You almost done?” he asked.

Sam nodded.

“Good. I’ll finish his whipping.” Before Sam could protest, he continued, “Grab the paddle. If Daddy thinks his ass hurts now, he’s in for a huge surprise.”

Sam kept up the brutal pace, fucking his fingers into his father’s ass until the whimpers had died down and the muscle was loose and pliable. One last rub against his prostate and Sam pulled out completely to retrieve the vibrator they’d bought just for today.

It was larger than any of their cocks at a whopping ten inches, and its highest vibration setting would have had Sam’s teeth chattering just holding the thing. As it was, he had some trouble getting it past the stubborn muscle of John’s ass. It was too large and John was too tight, but Sam forced it, adding more lube as he went, until it slid in much more easily.

John’s muscles were all rigid while he accustomed himself to being impaled. He didn’t bottom often, but when he did, he remembered just how much he loved the stretch of his ass and the stimulation of his prostate, even with the large amounts of pain both boys were intent on giving him. It merely added to his pleasure.

“Don’t lose it,” Sam said once it was all the way inside. Then he turned the vibration onto the lowest setting and stood back to watch as his father bucked against his restraints, trying to find some kind of friction.

He was so entranced with his father’s wanton display that he forgot about Dean until the telltale sound of a cracking whip broke his concentration. It was barely deep enough to break skin, but unlike Sam’s previous blows, this one drew a small drop of blood that had Sam wishing he could come.

They’d both agreed on this earlier, but Sam didn’t have the guts to make their father bleed.

Dean seemed to enjoy it, though. All five strikes broke skin, tingeing John’s back with red blood. Sam had a sudden urge to lick it up, but settled on readying his paddle instead.

“Such a good Daddy,” Dean praised, running his hand down John’s leaking back. “Staying quiet through your punishment. Still more to come, though.”

Sam took aim and waited for Dean.

Dean quickly unstrapped the gag from behind John’s head and pulled the phallus from his mouth.

“Tell me, why are you being punished?”

John looked down in shame and answered. “For talking and yelling through my gag,” he said.

“Eyes on me,” Dean ordered, his voice angry.

John’s eyes shot up of their own accord.

“Why are you being punished?” he asked again.

“For talking and yelling through my gag.”

Dean nodded. “Count. You have twenty-five.”

John jerked hard against his restraints as the paddle came down, easily hitting both of his cheeks and jostling the plug inside of him. He groaned long and loud, his prostate sending spark after spark of pleasure up his spine.

Dean’s hands pulling his hair got his attention.

“I said _count,_ ” Dean emphasized as Sammy brought the paddle down again.

“ _Two!_ ” he yelled.

“No. You don’t get to continue when you didn’t count on cue. Start over.”

Sam wound up and brought the paddle down as hard as he could on his father’s ass, loving the pained sound that came from him when he screamed, “ _One!_ ”

“Good,” Dean praised. “And that’s ten more for disobeying an order. You have thirty-five.”

John whimpered, but obediently counted, “ _Two!_ ” when he felt the paddle again.

 _“Three… Four… Five…”_ John gasped, trying to breathe with haggard lungs. “ _Ten!”_

“You’re doin’ good, Daddy,” Sam said, switching out the large paddle in his hand for a different one. It was just smaller than a ping pong paddle, but squared off and a slightly longer.

This time, John heard the whistle of air as the paddle smacked his bare thigh— _“eleven!”_ —before it moved immediately to his right—“ _twelve!”_

It was more painful than the previous paddle, though he could tell it was much lighter. It sliced through the air, the smacks stinging, leaving a burning throb that made the skin so, so sensitive.

His back tingled with every movement from the whipping; his ass and thighs were going to be bruised for days; his wrists, elbows, ankles, and knees were nearly rubbed raw from his struggles; and his lungs were struggling to pull in air as he sobbed from the pain.

Still, he couldn’t deny his arousal with his cock hard and leaking, ignored by his boys, but straining against the cock ring with a need to come. The phallus inside of him jerked with every hit, slamming into his prostate with its vibrating head, sending shivers of pleasure throughout his body, masking the pain.

No part of his backside was left out, the paddle making its way thoroughly across both of his cheeks and thighs.

“ _Twenty-five!_ ” he nearly sobbed, tears already coursing down his face to drip on the floor beneath him.

The hits stopped then, and relief coursed through John at the knowledge that they were giving him a short reprieve before continuing his punishment.

“Doin’ so good for us, Daddy,” Dean said. His hand came up to toy with John’s sack, rolling it between his fingers.

Sam hummed in agreement, his small footsteps coming closer until he came into view. He passed Dean the paddle and dropped to the ground beneath John. A small smile was all John could see before he closed his eyes in ecstasy as Sam took him into his mouth, sucking and moaning for all he was worth.

“You could’ve come by now,” he paused to say. “But you had to be bad.”

John couldn’t even think of a response as the wet heat of his boy’s mouth found and suckled his head. He barely even remembered to count—“ _twenty-six!”_ —with his brain malfunctioning as Dean let the paddle fly directly against the phallus in his ass.

“Good, Daddy,” Dean praised, surprised that John was still able to count.

One after the other, the remaining nine strikes were taken out on John’s ass, each one harder and quicker than the last.

“ _Thirty-five!”_ John screamed, thrusting as much as he was able into Sam’s mouth while the boy moaned his appreciation.

Dean was at his ass then, grabbing the phallus and fucking it in and out of John’s ass, making sure to angle it just right to have him writhing against the bindings. His other hand skimmed his father’s back and thighs, slipping beneath to tug at his sack—Sam’s signal.

John felt Dean scratch lightly at the heated flesh, nails dragging against sensitive skin, and then the dreaded cock ring was gone, his rising orgasm only held back by sheer force of will.

“Come for us, Daddy,” Dean said, placing a hard smack on his ass.

John was done for.

Harder than he ever had before, John came into his son’s mouth, screaming his release as pleasure coursed through him, triggered again and again by the throbbing pain at his backside. His vision swam, and John blacked out by the force of it.

The last thing he heard before he was completely out was his sons’ voices in his ear.

“Such a good Daddy,” Sam said.

“The best,” Dean agreed.

And he was gone.

**Notes for the Chapter:**

> And wasn't that enjoyable? I know I had to take a couple of /breaks/ in between writing this chapter. The next chapter will go up tomorrow. It will contain the final piece of plot for this fic. Sad to see it end? No worries. The next fic will go up July 4th, regardless of working internet or not. Worst case, I'll post that shit at the nearest Starbucks. Comment your happiness, people! And kudos your enjoyment :)


	5. Aftercare

**Summary for the Chapter:**

> It's the next morning. Dean's guilty. John's caring. Sam's just horny.

**Notes for the Chapter:**

> Final chapter everyone! It was supposed to be more plot, but it kinda ended with some relatively vanilla sex instead. I'd apologize, but I don't think those screams are complaints. Do you? If so, don't forget to comment them! Enjoy ;)

When John came to, he was lying on his stomach with two angels surrounding him. Soft fingertips wound their way through his hair, petting him lightly, while something soothingly cold was massaged gently onto the skin of his backside. His wounds were dressed, and his muscles were loose and limber, the ache a comfortable feeling after such an intense scene—hell, _three of them_. He would have been content to stay where he was had his mind not tuned into the hushed conversation.

“Dean, stop freaking out, okay? He’s fine.”

“He’s freaking _bleeding_ , Sam. _I_ did that. How could— _fuck…_ ”

“It’s not even bad. Look. They’re barely more than scratches. Gone in three days, tops. Besides, it was on his list, remember? You didn’t even go that far.”

The silence he was met with was enough for John. He blinked his eyes open, trying to unblur everything around him and settled on rubbing his hand over his face. He picked himself up onto his forearms and pulled his legs under him so he could sit on his knees—the only comfortable sitting position he would have for a while.

“Hey, Dad!” Sammy said, smile blinding.

Both of the boys’ makeup was gone, and the only clothes they had on were their birthday suits. He wasn’t disappointed in the least at the sight. “Hey,” he said, sleep still in his voice. He cleared his throat and tried again. “You boys did so great. I’m proud of you.”

“Do you hurt anywhere?” Dean asked, ignoring the praise.

John almost frowned. “My back stings a bit, but it’s my ass that’s sore. Been a while since I’ve taken it.” He smiled then, but Dean didn’t respond. “How about you boys? I was kinda rough with you—especially you, Sammy—but I left my cock in Dean quite a while. You okay?”

Sam kept the smile on his face. “I’m _awesome_.”

Dean just nodded quietly.

John fingered Sam’s cock cage, and the boy hissed with a mixture of pain and pleasure. “Does it hurt?” he asked.

Sammy shook his head. “Just sensitive. I wanna come so bad.”

“How about you, Dean?”

Dean bit his lip. “It feels like it’s got a chokehold on my cock. Can’t get hard for nothin. I like it though.”

John nodded, completely aware of Dean’s withdrawn disposition. He quirked an eyebrow and Dean smiled, but his face was tight, screaming _I’M SORRY!_ without having to speak a word.

“Dean,” John chided.

Dean looked down and John pulled him limply into his arms, cradling his head and petting him lightly. “You did so good,” he said. “Gave me exactly what I wanted.”

“You got hurt,” Dean murmured against him. “And I liked it.”

“No,” John comforted. “I got punished, and you liked it. We _both_ did.”

“I went too far.”

Sam scoffed, but John cut off his argument with a quick glance. “Do you trust me, Dean?” John asked seriously.

Dean looked up at him, confused. “Of course,” he answered.

“Good. And I trust you too, both of you.”

“You shouldn’t,” Dean said sullenly, looking down in shame. “I hurt you.”

John pulled his chin up and pressed their lips together in a comforting kiss. “If I told you to stop, would you?” he asked, pressing in for another light kiss.

Dean nodded, unable to speak with his father’s mouth molding itself to his own.

“Then there’s no problem,” John said, smiling and pulling back to look Dean in the eye. Dean really needed to hear what John said.

“Yes there is!”

“No, there isn’t. If I wanted you to stop—if you were _really_ hurting me—then I would have signaled you, and you would have stopped.”

“But I liked it,” he forced out. That was the real problem. It was one thing to draw blood, quite another to want to see more of it.

John smiled amusedly. “You were supposed to like it, Dean. If you don’t like it, I don’t like it.”

Dean bit his lip again, still conflicted, but not anywhere near where he’d been before. “You sure?” he asked.

“One hundred percent. Sammy liked it too. Didn’t you, Sammy?”

Sam nodded, nearly bouncing on the bed. “It was so hot, Daddy, seeing you tied up like that. Sexy as _hell_ watching you writhe for us. I wish I coulda fucked your ass right then and there, but Dean said I have to wait two more days.” He looked down at his cage in anger, but there was some heat in the gaze too so John didn’t read too much into it.

“See,” was John’s response. “Everyone’s good.”

Dean had small smile on his face and John counted it as a minor victory.

“You took real good care of me, boys,” he continued, crushing his mouth against Dean’s, not holding back like he had before. He slipped his tongue inside, running it over the slick white teeth.

Dean gasped into the kiss, and moaned his pleasure.

“Such a good boy,” John said. He parted Dean’s legs so Dean was straddling him from below. “My princess,” he said, kissing deeply once more until Dean’s legs wrapped around his waist in an effort to lessen the distance between them.

John smirked and pulled back just long enough to line up and slide his cock into his son’s loose hole, still slick with come and lube from last night’s excursions. Dean hiccupped in surprise, but immediately set about driving John deeper inside of him until he could feel his father’s thighs press tight against his.

John’s eyes rolled at the feel of his boy’s hole on his swollen cock. Unable to think, just acting on instinct now, he reached out and pulled Sammy in until he was seated in front of him, chest to chest, straddling Dean’s stomach. He thrust slowly now, wanting to savor the moment, the feel of Dean’s tight ass around him.

Sam smirked and latched onto a nipple, causing John to gasp. His fingers came up to absentmindedly pinch and prod the other one while his brother fucked himself on their father’s cock. John was gasping and groaning, the slick and slide of Dean and the sparks of pleasure of Sam at his nipples overwhelming him.

Sam bit down hard and licked the reddened flesh, relishing in the cry his father let out at the movement.

“ _Fuck_ ,” John gasped. His hips stuttered, muscles twitching when his orgasm caught him by surprise.

Dean screamed when the flood of come sent sparks of pleasure through him in time with his father’s release, his cock still soft but making a valiant effort to rise.

Sam continued to toy with John’s nipples as he pulled out of Dean and collapsed back onto the bed, not caring that he could feel the marks on his back with every movement.

“Holy _fuck_ , baby doll,” John gasped.

“Your nipples are sensitive, Daddy,” Sam said, tonguing at the one he bit.

John just chuckled. He pulled Dean closer and wrapped them both in his arms. “Feel better, princess?” he asked.

Dean blushed, but looked at him, eyes sparking. “Much better, Daddy,” he said.

“Good,” John said. “Get some rest. Sammy gave us a few days before another Hunt comes callin’ and I wanna fill you both up before then.”

Both boys squirmed, wiggling closer, before closing their eyes obediently.  

**Notes for the Chapter:**

> And that's it. End of fic. The next "Holidays with the Wincesters" fic will come on Independence Day, the 4th of July, 2014. Rain, sleet, snow, or lack of internet shall not keep me from posting, so tune in then :)


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